Greg, since you have time on your side the best thing you can do is join your local sailing club and sail with others. Join a racing crew and get some miles under your belt. Racers do not let inclement weather stop them from sailing. In five years of racing you'll sail in a wide variety of weather condiditons and get invaluable experience.

Different boats have different characteristics. Mono's heel but I've sailed them so long I don't notice, multis don't heel but have a quicker motion that does bother some. Cruising multi's and mono's of the same size will have about the same passage times contrary to the claim of a multihulls blazing speed. Multis can sail in shallower water, make a better party platform, don't sink like a mono but can capsize although it is rare.

I also am not a DIY fan Greg, but over the years I've occasionally surprised myself when I've successfully fixed 'stuff'. I've generally found that if I see somebody fix something one time and pay attention/take notes then I can duplicate the work as and when necessary. If you want to cruise the Caribbean (or further afield) you're going to have to be able to make basic repairs.